Dress up anal, masturbation, forced

Chubby fat ass… That was my apt nick name..
Being all of 4,11 at 13 and due to eating way too much I was a chubby kid with a fat ass and moobs.. My mum just said I was big boned like her and my elder sister.. But looking back I wasn’t I was just a fat kid..
I didn’t have a lot of friends and as for me dating not a Chance I wasn’t a bad looking kid with auburn wavy hair and blue eyes but girls want tall guys and a slim body..
My sister had started to actually slim down.. And added curves to her 16 year old body.. Still had a big ass but her boobs where def her best asset… And she used to love to flaunt them…
Chad had been my only real friend for years..
And he lusted over my sister for years.. We Where hanging in my room, playing video games and watching porn on our phones.. he started talking about how hot my sister had become since she had grown up.. And how he would love to fuck her.. I could see he had a hard on.. As we lounged about he kept touching his cock through his jeans..
I told him he didn’t have a chance.. And the banter carried on and on as teenagers do
It was coming up to Halloween and we were discussing costumes.. I told him I didn’t have any money for anything fancy.. So I was going to have to just miss out on the fun..
He looked at me and said why don’t you dress up as a school girl.. Your sisters old clothes are bound to fit you if she has any about.. And you look like her when she was your age.. Even you tits are pretty close..
This led to me arguing and telling him to fuck off.. We ending arguing even more and he left for his house.. It was just an idea was his parting shot they don’t call you chubby fat ass nothing..
Even though I was upset he had planted a seed in my head..
And the next day I went trawling through the attic for any old clothes I could find.. My mum threw very little out and I did unbeknown to my friend actually were the same shirts and jeans my sister wore to our school when she was my age..
I found an old blue gym skirt a few pairs of blue knickers sports type bra and red blazer up in the attic..
I smuggled them into my room.. Shutting myself away to try them on..
The bra was a pull over thing and fitted my man moobs pretty well giving me a cleavage of sorts.. When I felt my moobs in them I could feel my 4 inch cock beginning to harden and imagined I was stroking a girl from school.. The tight blue pants tried in vain to contain my hard on.. The material was a lot softer than my budgie smugglers.. And it felt great against my throbbing cock while also holding my balls snuggly in place.. I ran my hands over my fat ass.. Looking over my shoulder I could see a girls fat bottom… I slid into the short pleated gym skirt.. I could feel my cock trying to escape.. If I bent over I could see the bottom of my ass cheeks…my cock was hard now.. I reached under the blue skirt and started to stroke it through the soft material.. I laid on the bed and looking down I could see the body of a young chubby girl.. Apart from the buldge in the skirt…. I lifted the skirt away and wrapped my hand around my cock.. Wanking it hard.. Through the cloth.. My hand found my tits and I was feeling them.. As I then slipped my hand down the blue knickers.. Finally taking my hard naked cock in my hand Wanking harder and harder till I came inside them… I had never came so much the knickers where covered and wet at the front… As my heart subsided….. I didn’t know why I was turned on so much… But I knew I had to explore a little more.. I stood on shaky legs.. Looking for something to clean my cum covered hand.. For some reason I started to lick it off I had tasted my cum before but this felt very dirty and different.. I carried on dressing adding the shirt tie and red blazer.. In the mirror I was almost a double for sister..the knickers where still wet, so I got an old tshirt lifted the skirt once me and rolled the knickers down.. Cleaning my self up as best I could as moved the skirt swished against my naked ass cheeks and my cock started to grow once more.. I felt my ass cheeks with one hand while I wanked again with the other… It took a lot longer to cum this time.. But eventually a small dribble came from my cock onto my hand once more I cleaned it off with my tongue..
It was getting late so I undressed and hid the old clothes.. But stepped back into the knickers the wet patch settling over my cock and balls.. Climbed into bed and was soon asleep… I woke up with morning wood.. And stroked my cock till I came inside the knickers once more..
I heard my mum shouting me so I got up and hid the wet knickers, got dressed for school and off I went..
Chad was waiting for me by my gate and we soon made up and off we walked.. I told him I had thought about the idea and maybe it would work.. I didn’t tell him anything else we left it there..
As it was Friday my mum would be going out with her friends and my sister would be going for a sleep over..
So I knew I had all evening to try on my sisters old clothes again every time I thought of it my cock started to get hard.. And I had to sneak off for a quick wank in the school toilets..
Rushing home I found my house empty.. The typical latch key kid.. I wolfed dinner down and was soon upstairs.. My cock and balls where crusty with cum so I decided a quick shower before my next experiment.. As I was soaping my cock and balls my hand kept straying underneath them.. My soapy fingers grazed over my ass ring.. For some reason I tested it tightness and my finger popped inside… Pushing it way in… I loved the feeling it didn’t hurt was just a strange sensation of being full.. Almost like having a shit… I added more soap and it slid in easier I was finger fucking my ass.. My four inch cock was again rock Hard..
I had sprouted a few hairs around my cock that I was rightly proud of.. As I didn’t have hardly any hair any where else.. But.. I noticed the hair remover on the shelf in the shower and decided to try it… I spread over my legs, crotch and balls… And left it for the desired time.. I could feel it tingling as I washed it away I was silky smooth all over.. My cock looked bigger naked.. Wrapping myself in a big towel I went to my room and turned some porn on my pc… Looking for xdressing.. To inspire and learn from.. As I laid my sisters old school outfit on the bed..
I heard a loud knock at the front door.. I tried to ignore hoping they would go away….but it was persistent.. I turned off my pc screen.. Wrapped my dressing gown around me and went to the front door.. Chad was stood on the step looking miserable tears running down his face.. He have a go at you again? I asked, yes he’s been down the pub again..
He being his step father..he hated Chad but loved his mother.. And seemed to resent chad being in his life..
Better come in dude.. He walked past me…. It was a little awkward I was still naked under the dressing gown.. Even though it covered most of me.. It stopped above my knees.. And the smoothness of the cloth against my shaved skin.. Was making my little cock twitch…
I’ll go and get dressed I stammered…
Chad looked at me suspiciously, Dude..why are you dressed like that.. You been wanking over porn again.. I gotta see
With that he ran upstairs and burst into my Bedroom… Wow is this all your sisters old stuff…
Where you going trying it on??
I followed him in sheepishly yes it was your idea.. After all!
Cool let’s see it on you..
He flopped down onto the bed and started to finger the cloth on the short skirt… Aren’t you going to leave so I can get dressed I asked
. Why are you shy I’ve seen you naked many times..
I know but this feels different some how..
Na he said get on with it let’s see you dressed up..
Well just pass those blue pants… He threw them over to me and I slid them on under my robe.. Not wanting him to see I had shaved around my cock and balls.. I don’t know why I just didn’t want him to think I was queer or something else..
I dropped the robe and smoothed my pants over my ass praying my cock would stay down..
He passed me the bra I slipped it on over my head and squashed my moobs tightly in side..
Wow he said you really do have tits..
If you carry on taking the piss I’m stopping..
No you look great please carry on.. You actually look like a girl already.. I quickly put on the shirt and skirt tucking it into the waist band.. Then the blazer…
Chad stood up. And walked around me appraising me from every inch..
Wow dude you look just like your sister… When she was a bit younger..
Did you shave your legs they look really smooth… Yes I whispered I wanted to get into the feel of it.. Thought it might be better.. Bend over the bed let me see.. His tone was very low but it felt very authorative…
I bent over and put both hands on the bed.. My skirt rode up showing my ass.. And the bottom of my thighs..
Wow you really do look like a girl from behind.. I felt his hand hesitantly reach out and stroke my legs.. At the top by the hem of my knickers.. So smooth… Dude so smooth.. Both of his hands where roaming over my legs.. Then s fingers slid up the hem of my pants.. Really really smooth.. I stood motionless as he felt me up.. Then his hands felt my ass squeezing it gently.. Dam… You really do look like a girl.. I could hear the wonderment and lust in his voice… He stepped closer rubbing his crotch against my ass…
Chad what are you doing..
Shhhh he said you look amazing… So beautiful I didn’t realise how sexy you would look. His fingers pushed the knickers up either side so my cheeks where naked to his touch..
So sexy.. He just kept feeling my ass and legs… My cock was hard as nails trapped inside my knickers..
Chad.. I think you need to stop..
Nooo I want to carry on feeling you up your skin is so smooth…. He pushed my body further down onto the bed..throwing the short skirt up over my back, My ass now was almost naked.. His fingers did feel wonderful against my skin…
He knelt down behind and actually started to kiss my arse cheeks biting licking each one.. So fucking sexy Sandy.. Your so sexy so smooth .. He was lost sandy is my sisters name… I reached down and had to free my cock..
Chad pealed down my pants and parted my cheeks… His face was soon buried between them licking my ass cunt… And I felt his hand on my cock. So smooth and tasty sandy… His tongue Seemed to climb up inside my ass… He wanked my cock… Then started licking my balls and skin between my legs.. I felt a finger enter me… Smooth and easy my ass gripping it As it slowly fucked me.. His tongue returned to my ass as he stood he had lowered his jeans without me knowing.. His tongue and finger left me and I felt empty.. His legs where directly behind mine as I felt him lean in.. And he spat on my puckered ring..
Sandy in going to fuck you.. His cock luckily I found out later was slimmer than mine… His head hot naked cock head pressed against my ass held onto one ass cheek…
I felt my ass open up and he was inside the pain
Was immense even though his cock wasn’t the biggest my knees started to buckle and he followed me as I collapsed onto the bed… That was all it took for him to fill me with his cock… His hairs where against my ass as he mumbled sandy in inside you.. His cock was moving in and out and it didn’t take long for both of us to lose our virginity that day…

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